This invention relates to the synthesis and methods of using a drug, deuterated L-DOPS, to treat deficiencies in the neurotransmitter norepinephrine. This classic neurotransmitter has roles in both the brain and the periphery. In the brain, norepinephrine is thought to play important roles in attention, memory, sleep, pain, movement, distress, and mood. Outside the brain, norepinephrine mediates regulation of the circulation by the sympathetic nervous system by increasing blood pressure.

Oral norepinephrine is ineffective in treating deficiencies because the gut-blood and blood-brain barriers effectively block this neurotransmitter from crossing. A norepinephrine pro-drug (L-DOPS, droxidopa, Northera) is being developed for treating deficiencies of norepinephrine. While L-DOPS can induce the synthesis of norephinephrine, the produced neurotransmitter is rapidly degraded into toxic byproducts. Substituting deuterium for the hydrogen in L-DOPS, deuterated L-DOPS, decreases the ability of the synthesized norepinephrine from being degraded.